Bob Wingate's Blog: Submitting to The Paperboy

I wish I had an illustration for this story. The artist Sean would have done a beautiful job, if only I'd published it back in 1999. Better no photo or illustration at all, than one that won't do the story justice. Use your imagination, guys.

The Paperboy
Part 2

It was the next Saturday that Rob came to collect, dressed as usual in his arousing, skimpy, too tight outfit and wearing a pair of sweatsocks under his white Converse All Stars. He told me his folks were away for the weekend, and that we were going to have some fun at his house this time.

Rob told me that we were going to jog two miles before going to his house, which was only three blocks away. Being a typical hot, muggy summer evening, we worked up quite a sweat by the time we finally got to Rob’s house, where we immediately went downstairs to the basement game room with wet bar. It was a really nice big brick colonial befitting his father’s very successful law practice.

Rob went into a small room behind the bag and returned with a gym bag. He opened it and removed a 2" wide dog callar with ½" spikes on the outside and ¼" nubs inside (I wondered where a kid his age acquired his ideas and equipment, but was unaware then that I’d eventually find out) and a pair of handcuffs. The collar was put around my neck with the cuffs placed inside the collar positioned behind my head, and buckled closed.

Rob flopped down on a couch, commanded me to kneel down before him and remove his sneaks. I went down to use my teeth to untie the bow and loosen the laces. I placed my chin around the back of each shoe, trapping it between my chin and chest so I could pull each one off. Being in such close proximity to his sweaty, funky-smelling socks and feet from our two-mile jog was a real turn-on that caused my prong to harden and juice precum copiously. The scene proceeded pretty much as that first scene at my house described earlier. We both seemed to enjoy a foot fetish as I eagerly tasted and removed Rob’s socks, then bare feet.

Rob clasped his hands behind his head to expose his sweat-soaked armpits. I could smell the ripe smell and was ordered to lap them. Pits are also a fetish of mine (even though his had virtually no hair, as I said before), so I had no qualms about doing them; in fact, I wanted and had to do it! They were delicious.

I was directed onto his chest to lick, vacuum and nip at the tit crowns on his chest as they erected to hard little sensitive points. Down his chest to his indented navel, my tongue, teeth and lips did all they could to arouse Rob sexually.

He told me to place my head between his muscular, sweaty thighs. The smell of his perspiration, precum, urine and even ass-musk combined to make a stimulating aphrodisiac to me. My own dick was rock-hard and oozing liberally its precum juices tenting out and wetting my shorts. Rob told me to strip off his stretched shorts which I had to do orally as my hands were still cuffed behind my head.

My teeth bit into the front of the waistband and pulled down. Rob stood up to afford me access and continuously work all the way around his body with my mouth so my teeth could pull the waistband out over his bulging jock and asscheeks, then down his muscular legs. I finally got them down to the floor so Rob could step out of them.

Now my godlike master Rob was standing in front of my kneeling body wearing only his stinking, sweat-sodden, cum- and piss-stained jockstrap. I was getting to the point where I worshipped, idolized and adored this young stud and would do virtually all, if not everything he ordered me to do.

He ordered me to strip off the funky jock orally as before, since my hands were unavailable. This being done, Rob ordered me to lie on the floor on my back and spread my legs. He brought over a four-legged barstool from the wet bar and placed it between my legs, with one leg located snugly at the juncture of my legs by my crotch. He lifted up my scrotum so he could jam the leg right up into my crotch.

Rob got two shoelaces, tied a slipknot in each, and carefully slipped one “noose” over each of my balls, tightening each so it wouldn’t slip over and off the gonad it was attached to. He took the loose end of each lace and pulled it around the wooden leg of the barstool to stretch and descend each nut separately deeply into its half of my ballsac. The tension (sexual and physical) of this ball-separation and –stretching was incredibly exciting; I was able to raise my head enough to see the shiny, purplish-red skin drawn tightly over my orbs, which really turned me on.

My hard dick was throbbing with my heartbeat and was spewing precum in an almost steady stream as it lay flat on my belly pointing to my navel. Rob now got some cord (like from an old Venetian blind), placed my prick upright against the stool leg, tied an end around the base of my tool and the leg of the stool, and proceeded to wind the cord around and around my dick and the leg right up to the bottom of my glans. Now my rigid pole was securely lashed for its full length up along the piece of furniture.

Next Rob got a couple of spring-type clothespins which I immediately knew their purpose. He knelt down to suck my nipples to arousal. They were very cooperative, after which he pinched them to inflict additional pleasurable pain, as well as dry them of his saliva prior to his placing a pin on each of my tit-crowns.

I then had to sit up so Rob could attach a cord to one of the clothespins, put it around the leg a few times, and then tie it to the second pin. This effectively bound me sitting upright to the barstool and eliminated my ability to back away from it.

I watched as Rob walked to the opposite side of the barstool and knelt down. He told me to roll over onto my left side, and as I did so he guided and leaned the barstool onto its side also. Now the stool and I were both positioned on our sides. Rob went back to the storage room and returned with a black dildo about 8" long by 1 ½" diameter with a round base, like a half of a baseball to rest on. He lubed it with KY-jelly, greased my anus with first one, then two, and finally three fingers; positioned its tip at my pucker and shoved it quickly and violently up inside me to its hilt. The initial pain and shock ebbed to a pleasant feeling of penetration and fullness.

Rob then assisted me and the stool back to an upright sitting position where the cleverly designed dildo’s round base caused it to constantly move around up in my shitchute and across my prostate with any type of motion on my part. I looked down at the shiny dark glans of my cord-wrapped, trapped penis to see a steady drizzle of precum issue from my gaping piss-slit.

I can’t begin to tell you how wildly turned on I was. I was also very curious about how and where Rob might have gotten these ideas—mind you, I certainly wasn’t complaining; I loved them!—as well as how this young a kid had access to and accumulated the equipment such as the dildo. I didn’t know it at that time, but I was eventually going to learn, much to my joy!

Now sitting up, he bent my legs at the knees and brought the soles of my feet together facing each other. A shoelace was used to tie my two big toes together, then more laces were used to lash together the rest of my toes. He tied the corresponding toe on one foot to the other foot as well as using “figure eights” to bind them together. Also, the heavier cord was used to tie around my ankles to the leg opposite the one to which my fuckstick was bound.

Naked, Rob sat down with his back to me on the stool. He leaned forward to display and spread open his buttocks to expose his asscrack which as usual was not perfectly wiped! Instantly, and without instruction, I immediately knew what was expected of me. I leaned forward to kiss his asscheeks, stick my nose into his musky crack, used my teeth to pull at the tiny “dingleberries” of dried pieces of shit residue caught in the hairs in his asscrack, then finally let the flat top of my tongue lap the length of the crease between his buttocks before stiffening it to probe into his anus, penetrating past the muscle ring of his sphincter and up into his rectal cavern. Yummy!

Rob’s hard-on was trapped between his belly and the cushion on the barstool as I continued to minister to his rectum until I felt him stiffen with his sphincter clamping tightly on my tongue. He spasmed 7 or 8 times, and as he raised up off the stool I saw a copious pool of his jizz on the cushion and his stomach.

Rob’s dick was still hard as steel despite his recent ejaculation. He turned around to face me and sat down on the barstool with his slimy rigid poker just inches from my face. I dove for it, but was rewarded with a sharp, stinging slap across my face with the admonishment that I was to do absolutely nothing to or for him unless commanded to do so!

Now Rob ordered me to tuck his rod under my chin to pull it away from his belly so I could lick the love goo from his first climax drying there. I was then rewarded for my patience when he ordered and allowed me for the very first time in all of our meetings to put my lips around the tip of his manhood. It was still wet with his first outpouring of spooge and was intoxicating. He grabbed the back of my head and slowly lowered it down the entire 7 ½" of his cockshaft until my nose was buried in the hair of his pubes. My throat opened to accommodate and welcome the impalement by the intruding manmeat.

My own 6" boner tied to the leg of the barstool and now tightly trapped between my body and the leg was being constantly stimulated in its roped, confined restriction. I was approaching my own orgasm quickly.

Simultaneously, Rob started pumping my head up and down on his fuckpole. I felt it get even harder and slightly larger just prior to its exploding another load of cream into my waiting mouth. I swallowed his offering greedily.

Within seconds I popped my huge load and pulled back to watch my thick, hot, creamy-white deposit of balljuice flow from my piss-slit and run down over the cord wrapped around my cock. Rob scooped it up and fed my cum to me. Rob and I were both exhausted, but supremely and ultimately satisfied.

He also told me that if I really and truly enjoyed what the two of us had done the last few weeks, that he and I could expand on it. That he could introduce me to other neighborhood kids—many of whom I already knew, but would never suspect had the same kinky interests. The group had several secret meeting places; additional, different “toys” and equipment; and further scenes that could be embarked upon. My obvious answer was “yes.” If you’re interested, I’ll write you about them. I found them most arousing and enjoyable.

If only I'd read and published this piece at the time. Is it too late, 17 years later, to say that I'm still interested?!—BW